O-Phenylenediamine → 3-(tert-Butyl)quinoxalin-2(1H)-one

HRID 1080885Notes

Reaction equation

HRID 1080885 reaction equation
[CH3:1][C:2]([CH3:9])([CH3:8])[C:3](=O)[C:4](O)=[O:5].[C:10]1([NH2:17])[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16]>C(O)C>[C:2]([C:3]1[C:4](=[O:5])[NH:17][C:10]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:16]=1)([CH3:9])([CH3:8])[CH3:1]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 13150Trimethylpyruvic acid

Product 1

HCID 233661883-(tert-Butyl)quinoxalin-2(1H)-oneYield 55.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 83 ml portion of ethanol was added to a mixture of 4.14 g of trimethylpyruvic acid synthesized in accordance with the method of Jaeger et al. (J. Am. Chem. Soc., pp.717-732, 1979) and 3.02 g of o-phenylenediamine. The thus prepared mixture was refluxed for 3 hours in an atmosphere of nitrogen. By concentrating the resulting reaction solution, 3.15 g of 2-t-butyl-3, 4-dihydro-3-oxoquinoxaline was obtained.

Workup

  1. temperatureThe thus prepared mixture was refluxed for 3 hours in an atmosphere of nitrogen
  2. concentrationBy concentrating
  3. customthe resulting reaction solution

Sources & evidence

ORD record
ord-1687eec6291b4f139893cae8f45aa146
Source dataset
uspto-grants-1996_12
Patent number
US05583227

Reaction notes

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